6-溴-4,4-二甲基-2-环己酮 | 40441-34-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 6-溴-4,4-二甲基-2-环己酮
• 英文名称: 6-bromo-4,4-dimethylcyclohex-2-en-1-one
• 英文别名: 6-Brom-4,4-dimethyl-2-cyclohexen-1-on；1-Oxo-6-brom-4,4-dimethyl-cyclohex-2-en；4-Brom-6,6-dimethyl-3-oxo-cyclohexen；6-Brom-4,4-dimethylcyclohex-2-enon；6-Bromo-4,4-dimethylcyclohexenone
• CAS: 40441-34-7
• 化学式: C₈H₁₁BrO
• 分子量: 203.079
• InChiKey: DLVSXQATBHXHBP-UHFFFAOYSA-N

物化性质

• 熔点：
  47.5-48 °C
• 沸点：
  232.5±40.0 °C(Predicted)
• 密度：
  1.362±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2914700090

反应信息

• 作为反应物：
  描述：

  6-溴-4,4-二甲基-2-环己酮 在 lithium carbonate 、 lithium bromide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 4,4-二甲基-2,5-环己二烯-1-酮
  参考文献：
  名称：

  一系列烷基-4,4-二甲基环己-2,5-二壬烯以及相关的环己酮和环己酮的制备及性能

  摘要：

  描述了4,4-二甲基-，3,4,4-三甲基-，3-乙基-4,4-二甲基-，3,4,4,5-四甲基-，3,4-三甲基， 5-二乙基-4,4-二甲基-，2,4,4-三甲基-和2,4,4,5-四甲基环己-2,5-二烯酮，以及相关的环己酮和环己酮。讨论了相关系列的2,6-二溴环己酮的立体化学，并比较了各种立体化学标准。给出了3,4,4-三甲基环己-2-烯酮的光谱数据；使用nmr溶剂转移和其他数据来证实该化合物的最近报道的制备中的主要产物实际上是3,6,6-三甲基环己-2-烯酮。

  DOI：

  10.1039/p19730000529
• 作为产物：
  描述：

  4,4-二甲基-2-环己基-1-酮 在 5,5-二溴巴比妥酸 作用下， 以 乙醚 为溶剂， 反应 2.0h， 以76%的产率得到6-溴-4,4-二甲基-2-环己酮
  参考文献：
  名称：

  Grundke, Guenter; Keese, Wolfgang; Rimpler, Manfred, Chemische Berichte, 1985, vol. 118, # 9, p. 4288 - 4291

  摘要：

  DOI：

文献信息

• A convenient, rapid, and general synthesis of α-oxo thiocyanates using clay supported ammonium thiocyanate
  作者：H.M. Meshram、Pramod B. Thakur、B. Madhu Babu、Vikas M. Bangade

  DOI：10.1016/j.tetlet.2012.01.113

  日期：2012.4

  A very rapid, convenient, and general method for the synthesis of alpha-oxo thiocyanates has been described by using clay supported ammonium thiocyanate. The procedure avoids the use of additional catalyst, solvent, aqueous work-up and the yields are high. Moreover, the method is applicable for a variety of aryl, heteroaryl, alkyl alpha-halo carbonyls, beta-keto tosylates, alpha-halo beta-dicarbonyl, alpha-tosyl, beta-dicarbonyl, alkyl halide, and alkyl tosylates. (C) 2012 Elsevier Ltd. All rights reserved.
• Halogenation of Enol Silyl Ethers. Synthesis of Various Types of α-Bromocarbonyl Compounds
  作者：L. BLANCO、P. AMICE、J. M. CONIA

  DOI：10.1055/s-1976-23987

  日期：——
• 5,5-Dibromo-2,2-dimethyl-4,6-dioxo-1,3-dioxane; A New Brominating Agent for Saturated and α,β-Unsaturated Carbonyl Compounds
  作者：R. BLOCH

  DOI：10.1055/s-1978-24691

  日期：——
• Functional group hybrids. Reactivity of .alpha.'-nucleofuge .alpha.,.beta.-unsaturated ketones. 1. Reactions with organocopper reagents
  作者：Thomas R. Barbee、Kim F. Albizati

  DOI：10.1021/jo00024a014

  日期：1991.11

  A series of alpha-nucleofuge alpha',beta'-unsaturated ketones encompassing a variety of structural types and nucleofuges was prepared. Treatment of these compounds with lithium dimethylcuprate or methylcopper leads primarily to either reductive cleavage of the alpha-nucleofuge or conjugate addition. Good alpha-nucleofuges favored the reduction pathway while poorer nucleofuges favored conjugate addition.
• Functional group hybrids. Reactivity of .alpha.'-nucleofuge .alpha.,.beta.-unsaturated ketones. 2. Reactions with malonate anion. Concerning the mechanism of the Favorskii rearrangement
  作者：Thomas R. Barbee、Hedeel Guy、Mary Jane Heeg、Kim F. Albizati

  DOI：10.1021/jo00024a015

  日期：1991.11

  The scope and limiations of the reaction of alpha'-nucleofuge alpha,beta-unsaturated ketones with sodium dimethyl malonate has been studied systematically. The substrates with good nucleofuges (halides, mesylate) give cyclopropanols upon reaction with malonate anion by way of a conjugate Favorskii reaction. In reactions with substrates containing the poorer nucleofuge (acetoxy) conjugate addition proceeded without entering the Favorskii manifold. Concerning the mechanism of the Favorskii reaction, it is suggested that the loss of the nucleofuge occurs to give a 2-oxyallyl cation, but that disrotatory ring closure is facile and the only products observed result from nucleophilic trapping of cyclopropanones to yield cyclopropanols in fair to good yield.